methyl cis-3-cyanocinnamate | 203512-53-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: methyl cis-3-cyanocinnamate
• 英文别名: methyl (Z)-3-(3-cyanophenyl)prop-2-enoate
• CAS: 203512-53-2
• 化学式: C₁₁H₉NO₂
• 分子量: 187.198
• InChiKey: BQJYULBYGRTLPZ-WAYWQWQTSA-N

物化性质

• 沸点：
  321.3±25.0 °C(Predicted)
• 密度：
  1.15±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  50.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl cis-3-cyanocinnamate 在 盐酸 、 甲醇 、 三甲基铝 作用下， 以 二氯甲烷 为溶剂， 生成 3-[(Z)-2-(2'-Sulfamoyl-biphenyl-4-ylcarbamoyl)-vinyl]-benzimidic acid; hydrochloride
  参考文献：
  名称：

  Design, synthesis, and SAR of substituted acrylamides as factor Xa inhibitors

  摘要：

  Substituted acrylamides were used as templates that bridge P1 and P4 binding elements, resulting in a series of potent sub-nanomolar) and selective factor Xa inhibitors. In this template, cis-geometry of P1 and P4 ligands is highly preferred. SAR on the substituting groups, as well as on modification of P1 and P4 moieties is described. Compounds in this series show good in vivo efficacy in animal models. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00199-3
• 作为产物：
  描述：

  3-氰基苯甲醛 、 O,O'-双(2,2,2-三氟乙基)磷乙酸甲酯 在 18-冠醚-6 、 双(三甲基硅烷基)氨基钾 作用下， 以 四氢呋喃 为溶剂， 生成 methyl cis-3-cyanocinnamate
  参考文献：
  名称：

  Design, synthesis, and SAR of substituted acrylamides as factor Xa inhibitors

  摘要：

  Substituted acrylamides were used as templates that bridge P1 and P4 binding elements, resulting in a series of potent sub-nanomolar) and selective factor Xa inhibitors. In this template, cis-geometry of P1 and P4 ligands is highly preferred. SAR on the substituting groups, as well as on modification of P1 and P4 moieties is described. Compounds in this series show good in vivo efficacy in animal models. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00199-3

文献信息

• Preparation of pyrrolidine and isoxazolidine benzamidines as potent inhibitors of coagulation factor Xa
  作者：John M. Fevig、Joseph Buriak、Pieter F.W. Stouten、Robert M. Knabb、Gilbert N. Lam、Pancras C. Wong、Ruth R. Wexler

  DOI：10.1016/s0960-894x(99)00164-x

  日期：1999.4

  critical enzyme in the blood coagulation cascade. Recently, the inhibition of factor Xa has begun to emerge as an attractive strategy for the discovery of novel antithrombotic agents. Here we describe pyrrolidine and isoxazolidine benzamidines as novel and potent inhibitors of factor Xa.

  丝氨酸蛋白酶因子Xa是凝血级联反应中的关键酶。近来，对于发现新型抗血栓形成剂的一种有吸引力的策略，已经开始抑制因子Xa。在这里，我们将吡咯烷和异恶唑烷苯甲as描述为Xa因子的新型有效抑制剂。
• AMIDINOPHENYL-PYRROLIDINES, -PYRROLINES, AND -ISOXAZOLIDINES AND DERIVATIVES THEREOF
  申请人：Bristol-Myers Squibb Pharma Company

  公开号：EP0934265B1

  公开（公告）日：2003-01-02
• US6057342A
  申请人：——

  公开号：US6057342A

  公开（公告）日：2000-05-02
• [EN] AMIDINOPHENYL-PYRROLIDINES, -PYRROLINES, AND -ISOXAZOLIDINES AND DERIVATIVES THEREOF<br/>[FR] AMIDINOPHENYL-PYRROLIDINES, -PYRROLINES ET -ISOXAZOLIDINES ET LEURS DERIVES
  申请人：DU PONT PHARMACEUTICALS COMPANY

  公开号：WO1998006694A1

  公开（公告）日：1998-02-19

  (EN) The present application describes amidinophenyl-pyrrolidines, -pyrrolines, and -isoxazolidines and derivatives thereof of formula (I), or pharmaceutically acceptable salt forms thereof, wherein one of D and D' may be C(=NH)NH2 and the other H and J1 and J2 may be O or CH2, which are useful as inhibitors of factor Xa.(FR) Cette invention a trait à des amidinophényl-pyrrolidines, -pyrrolines et -isoxazolidines ainsi qu'à leurs dérivés ou à leurs sels, acceptables du point de vue pharmaceutique, ces substances étant représentées par la formule (I) dans laquelle soit D, soit D' peuvent représenter C(=NH)NH2 tandis que H et J1 et J3 peuvent représenter O ou CH2. Ces substances sont utilisées comme inhibiteurs du facteur Xa.
• Design, synthesis, and SAR of substituted acrylamides as factor Xa inhibitors
  作者：Yonghong Song、Lane Clizbe、Chhaya Bhakta、Willy Teng、Wenhao Li、Yanhong Wu、Zhaozhong Jon Jia、Penglie Zhang、Lingyan Wang、Brandon Doughan、Ting Su、James Kanter、John Woolfrey、Paul Wong、Brian Huang、Katherine Tran、Uma Sinha、Gary Park、Andrea Reed、John Malinowski、Stan Hollenbach、Robert M. Scarborough、Bing-Yan Zhu

  DOI：10.1016/s0960-894x(02)00199-3

  日期：2002.6

  Substituted acrylamides were used as templates that bridge P1 and P4 binding elements, resulting in a series of potent sub-nanomolar) and selective factor Xa inhibitors. In this template, cis-geometry of P1 and P4 ligands is highly preferred. SAR on the substituting groups, as well as on modification of P1 and P4 moieties is described. Compounds in this series show good in vivo efficacy in animal models. (C) 2002 Elsevier Science Ltd. All rights reserved.